Jamaica A bamboo-walled hut, Lobster Trap (Sawyers Beach Rd., Hopewell; 876/783-5046; dinner for two $60) beckons travelers with its oceanside setting: rickety woven chairs overlook colorful boats and yards of netting. Crack open a fresh-caught grilled lobster, lightly seasoned with chef Derby’s special blend of jerk spices.
Nevis There are only 16 seats in the Mill at Montpelier Plantation Inn (St. John’s Parish; 869/469-3462; dinner for two $150), a stone 18th-century sugar mill, so reserve in advance for dishes like mahimahi roasted in plantain leaves, garnished with locally grown basil and sprinkled with brown sugar harvested on-site.
St. Martin A tiny spot on a quiet alleyway, Le Bistro Nu (Allée de l’Ancienne Geôle, Marigot; 590-590/879-709; dinner for two $80) has checkered tablecloths, wicker ceiling fans, and a Creole-French menu, from coq au vin and sea snails to steak frites.
Tobago The menu changes daily at the thatched-roof Kariwak Village Restaurant (Store Bay Local Rd., Crown Point; 868/639-8442; dinner for two $43), decorated with sculptures and paintings by local artists. Don’t miss the honey-baked chicken with grilled mushrooms and basmati rice.
Trinidad Surrounded by native artwork and an upbeat staff, Trinidadian celebrity chef Allyson Hennessy focuses on regional flavors at Veni Mangé (67A Ariapita Ave., Woodbrook, Port of Spain; 868/624-4597; dinner for two $50). Try the eggplant with pawpaw and plantains, and the homemade coconut ice cream for dessert.